Westport vacation rentals

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Top-rated vacation rentals in Westport

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Feb 24 – Mar 3

$102 per night

Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

Nov 27 – Dec 4

$122 per night

Guest favorite

Guest suite in Wilton

4.9 out of 5 average rating, 103 reviews

Serene Pond Views charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Feb 18 – 25

$120 per night

Guest favorite

Apartment in Westport

4.93 out of 5 average rating, 114 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

Jan 24 – 31

$155 per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Aug 7 – 14

$110 per night

Guest favorite

Guesthouse in Norwalk

5.0 out of 5 average rating, 113 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

Jul 3 – 10

$295 per night

Guest favorite

Guest suite in Norwalk

4.9 out of 5 average rating, 111 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

Jul 29 – Aug 5

$93 per night

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Nov 28 – Dec 5

$125 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Jan 23 – 30

$104 per night

Superhost

Loft in Bridgeport

4.86 out of 5 average rating, 173 reviews

Cozy Loft in beautiful St. Mary's by the Sea

Renovated cozy loft in beautiful St. Mary's by The Sea in Black Rock. Walking distance to award winning restaurants. Easy access to NYC/New Haven Metro North transit. Perfect for a weekend at the beach. Property includes 1 bed and a 78” sofa. Fully equipped kitchen with all major appliances, WiFi, & large TV. ***Please note that the ceilings are angled so taller guests (over 5’ 8”) might have to bend in certain parts of the loft.

Feb 1 – 8

$140 per night

Guest favorite

Place to stay in Westport

4.96 out of 5 average rating, 278 reviews

Sunny Westport 2 BR Retreat above Historic Mill

This eclectic, sunny, spot, sits above a renovated historic cider mill from the 1850s. It has been designed and furnished by our own team of artisans. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway is the perfect "Get Away."

Feb 1 – 8

$157 per night

Guest favorite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Aug 30 – Sep 6

$84 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Westport vacation rentals

Laptop-friendly workspace

Stay near Westport's top sights

Whole Foods Market22 locals recommend

Trader Joe's62 locals recommend

bartaco71 locals recommend

Shake Shack6 locals recommend

Black Duck Cafe13 locals recommend

Bow Tie Cinema Royale 66 locals recommend

Other great vacation rentals in Westport

Guest favorite

Home in Milford

4.98 out of 5 average rating, 153 reviews

Designer Beach Retreat on Exclusive Cedar Beach

Oct 10 – 17

$273 per night

Superhost

Apartment in Stamford

4.82 out of 5 average rating, 146 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Mar 20 – 27

$111 per night

Guest favorite

Apartment in Northport

4.92 out of 5 average rating, 129 reviews

Harbor Studio - Across from historic Northport doc

Jan 3 – 10

$111 per night

Guest favorite

Guest suite in Bayville

4.91 out of 5 average rating, 425 reviews

Romantic, Cozy and Private, 1 Block from Beach

Jan 10 – 17

$74 per night

Guest favorite

Guest suite in Greenwich

4.91 out of 5 average rating, 428 reviews

Charming Greenwich studio, 0.2 miles from train

Jun 28 – Jul 5

$176 per night

Superhost

Apartment in Stamford

4.88 out of 5 average rating, 162 reviews

High-Line Harbor Flat 2BD|Train|HarborPoint Access

Dec 31 – Jan 7

$116 per night

Guest favorite

Home in Centerport

4.96 out of 5 average rating, 112 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Jun 7 – 14

$629 per night

Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 508 reviews

Water front studio apartment with fireplace.

Sep 26 – Oct 3

$175 per night

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Other great vacation rentals in Westport

Guest favorite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Oct 11 – 18

$90 per night

Guest favorite

Cottage in Fairfield

4.96 out of 5 average rating, 141 reviews

Cozy Home away from Home!

Dec 16 – 23

$298 per night

Guest favorite

Home in Fairfield

4.96 out of 5 average rating, 289 reviews

Luxurious Barn With New England Charm

Mar 21 – 28

$236 per night

Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 34 reviews

Guest suite with private enter

Jul 10 – 17

$84 per night

Guest favorite

Apartment in Westport

4.92 out of 5 average rating, 13 reviews

Westport CT, Hide-away!

Jul 7 – 14

$157 per night

Guest favorite

Cottage in Westport

5.0 out of 5 average rating, 55 reviews

Wild Rose Cottage (Westport, CT)

Sep 29 – Oct 6

$300 per night

Guest favorite

Home in Westport

4.92 out of 5 average rating, 36 reviews

Gorgeous, luxury Cape in Westport!

Oct 7 – 14

$402 per night

Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 96 reviews

The Cozy Little Cottage

Jul 27 – Aug 3

$142 per night

Show all

Quick stats about vacation rentals in Westport

Total rentals
120 properties
Rentals with dedicated workspaces
80 properties have a dedicated workspace
Rentals with a pool
30 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
2.3K reviews

Frequently Asked Questions

Where should I stay in Westport?
Make yourself at home in Westport by choosing from our most frequently booked neighborhoods. We have over 220 vacation rentals in Saugatuck, over 160 vacation rentals in Greenfield Hill, and over 110 vacation rentals in Greens Farms.
Are there vacation rentals with a dedicated workspace in Westport?
Yes! Work meets play with ease at over 80 vacation rentals in Westport featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Westport?
Four-legged friends are welcome in Westport. Choose from more than 60 vacation rentals for guests traveling with pets.
Are there Westport vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 30 vacation homes with pools in Westport, available on Airbnb. Make a splash and soak up the sun in style!
Do house rentals in Westport have a bbq area?
Absolutely! We offer over 30 house rentals with a bbq area in Westport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westport have a gym?
Absolutely! We offer over 20 house rentals with a gym in Westport. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Westport have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Westport. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Westport?
Westport has more than 80 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

Westport vacation rentals

Top-rated vacation rentals in Westport

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Westport vacation rentals

Stay near Westport's top sights

Other great vacation rentals in Westport

Home in Milford

Apartment in Stamford

Apartment in Northport

Guest suite in Bayville

Guest suite in Greenwich

Apartment in Stamford

Home in Centerport

Apartment in Milford

Other great vacation rentals in Westport

Home in Stony Brook

Cottage in Fairfield

Home in Fairfield

Guest suite in Wilton

Apartment in Westport

Cottage in Westport

Home in Westport

Guesthouse in Wilton

Quick stats about vacation rentals in Westport

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Where should I stay in Westport?

Are there vacation rentals with a dedicated workspace in Westport?

Are there pet-friendly vacation rentals in Westport?

Are there Westport vacation rentals on Airbnb with pools?

Do house rentals in Westport have a bbq area?

Do house rentals in Westport have a gym?

Do house rentals in Westport have self check-in?

Are there family-friendly house rentals in Westport?

Destinations to explore